HCID 20471755, compound → HCID 20471699, compound

HRID 1388148Notes

Reaction equation

HRID 1388148 reaction equation
[CH:1]1([CH2:12][CH2:13][C:14](O)=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:1]1([CH2:12][CH2:13][CH2:14][OH:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 20471755HCID 20471755, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20471699HCID 20471699, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The starting material 3-cycloundecylpropan-1-ol is obtained as follows: hydroxymethylcycloundecane is reacted with thionyl chloride to give chloromethylcycloundecane, which is reacted with malonic acid diethyl ester in the presence of sodium ethylate to give (cycloundecylmethyl)-malonic acid diethyl ester, which, after saponifying the ester group and decarboxylating the corresponding malonic acid, gives 3-cycloundecylpropionic acid. 3-Cycloundecylpropionic acid is reduced with lithium aluminum hydride in tetrahydrofuran to give 3-cycloundecylpropanol.

Sources & evidence

ORD record
ord-d71d4b46b770417e9f495a21ae6ffb0f
Source dataset
uspto-grants-1984_02
Patent number
US04430339

Reaction notes

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